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The Art of Living – With Jesse Itzler (Episode 708)

On today’s episode The Art of Charm is honored to welcome back Jesse Itzler. His first podcast ever was The Art of Charm – and in today’s episode we catch up with him to learn what he’s added to his “life resumé” since we saw him last.

Some of our favorite life highlights include: signing a record deal, co-founding a private jet company, a beverage company, he wrote a New York Times Best Seller and he’s just released his latest book, Living With The Monks: What Turning Off My Phone Taught Me About Happiness.

Tune in to today’s episode to learn more about Jesse’s journey, and how first impressions and his unique mindset has enabled his unique successes.

The Cheat Sheet

What happens when you start to value the journey more than the outcome?

How does thinking about mortality help you channel self-confidence?

Why is Jesse more concerned about maximizing potential than being happy?

Please Scroll down for Full Show Notes and Featured Resources!

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More About This Show

In this discussion, we unpack Jesse’s mindset, specifically what is required to carve out such an impressively diverse life resumé. From being able to quantify and invest valuable moments wisely to valuing experience over planning, Jesse shares his keys to the kingdom.

So, Where Do I Start?

You’ve heard it at The Art of Charm before, but start with yourself. Jesse shares that works for him is quantifying his mortality. “No one’s here in 100 years!” Jesse exclaims, and this allows him to create a sense of urgency to embrace and take control of his own life experience and not fear failure.

Jesse shares, “the things I love to do, the window to accomplish things I want in my life, the window is shrinking.” Another creative way he’s challenge himself to grow is to invite 50 experts to teach him 50 new skills as he turns 50 years old later this year.

Stepping Into The Unknown

Jesse is honest about his biggest enemy – the voice inside his head that doubts his ambitions. He’s gone so far as to name him “Billy the Bully.”

“Once we get past limiting self talk, that’s where all the greatness is,” Jesse shares.

“To me, all the growth in my life—any success, anything—has come from stepping into the unknown,” Jesse explains.

While we might understand this sentiment, our lives are very scheduled. A full-time job demands us for a certain number of hours everyday, and our relationships can easily become stagnant if we don’t put energy and effort into them.

However, if we start disrupting our routine, then we can start conquering our fears.

Jesse explains, “The good news is for anybody—the more you face challenges, the more you go into the unknown, the quieter the bully gets. The bully only exists because you let him exist.” And that’s what he shares with his four children eight years old and younger

Building A Life Resume

What makes life interesting is our experiences. So often we might get stuck at a networking event measuring success by how many business cards we can collect or how many hands we shake.

But what would happen if we flipped the script to connect around our experiences, “it makes you a lightning rod” Jesse attests.

Because after an event, the business card may get lost, but a shared connection over an experience remains forever.

“The more of these experiences you put on your plate, the more interesting you become, the more you can offer the world, your kids, or yourself—and the quieter the bully gets.”

Praise The Effort, Not The Result

Whether it’s parenting or pursuing his next goal, Jesse has always valued the journey over the result.

One of Jesse’s current passions is ultra marathon running, and he advocates the power of even children accepting the challenge to run long distances because it requires planning, training, execution & maybe failure.

Especially failure.

Maybe our challenge isn’t a marathon, but Jesse reminds us that “our challenges have to be big enough to affect change.”

Whatever challenge you may be facing, try on Jesse’s manta, “remember tomorrow.” Ask yourself how you would feel tomorrow about the decision you made today.

On The Topic of Firsts and First Impressions

We find it so special that The Art of Charm was Jesse’s first podcast, as well as AJ and Johnny’s first guest interview.

Continuing on this month’s theme of first impressions, we get insight into impressions that have impacted Jesse’s experiences including his first impressions of the Russian Orthodox monks he unnecessarily shaved his head for and the intern-in-residence Lenny who he thought might break into his room at night.

He recalls a time he learned he didn’t make a great first impression, but how the impression he made was still authentic to who he is as a entrepreneur. And, of course, the first impression his wife made when all he had of her was a picture with an apple on her head.

Trying something for the first time is all about leaning into the unknown.

Jesse is no stranger to the unknown – most recently living in isolation in a monastery and capturing his experiences in his book: Living with the Monks.

When faced with shattered expectations, AJ asks, “how do you throw yourself in the unknown, and allow yourself to adapt.”

According to Jesse, adaptability comes from a place of gratitude, keeping an open mind, and leaning into the beauty of just experiencing.

Spoiler alert! Listen to the end of the podcast where Jesse reveals that his next book in the “Living With…” series might be with our own producer Jon Samnick, his lifelong friend from Roslyn, NY (“we grew up with several billionaires, sports team owners and guys who went to jail. there’s something in the water there…”)

We’ve offered the AOC house to them if we get to play it on Youtube for a month!